Created with Sketch.

Why Freedom is bad for entrepreneurs

Recently, I’ve been having a few discussions with business owners about the second point in my entrepreneurial hat trick. I’ve been meditating on freedom – that glorious, abstract stuff that goes with wealth and sanity like tom goes with dick and harry.

Turns out that the pursuit of freedom has been tripping up well meaning, ambitious entrepreneurs. Wealth and sanity have vanished in the face of the wannabe entrepreneur’s desire to live without rules or boundaries.

Yes, freedom might just destroy your business. Read on to find out why. Learn what can be done to ensure freedom never shatters you.

The freedom to do whatever you want

Every entrepreneur I meet confirms a the same beginning to their entrepreneurial journey.  It happens when they realized they just cannot work for someone else. The moment of this specific realization is universal among entrepreneurs with just one exception – dynastic family business owners who are born into entrepreneurialism.

Of course, a business is seldom started just to avoid the nine to five grindstone. Ideas are tossed around, passions are discovered and models are tested… but that process of finding “the thing” kicks off the moment an entrepreneur decides to quit their job.

Entrepreneurial folks love not having regular jobs. When you’re the only boss, you have total control over your schedule, deadlines, time and location.

Want to work from a cafe? How about the beach? Do it!

Feel productive working from 10pm to 3am? Screw office hours – do it!

It sure is good being an entrepreneur.

Once you start shooting for the business owner’s hat trick, freedom becomes almost instantly attainable.

Instant freedom – the double edged sword of the self employed

When you quit your job, you instantly win freedom. The moment you leave your boss’s office, your time is all yours. It feels great!

The problem is the moment you quit the job, it’s time to start pursuing your dream. It’s time to start rocketing toward the hat trick, while changing the world for the better!

Except you just won freedom. Best enjoy it for a little bit, right?

Why not take a few days to chill out at home and “brainstorm”? After all, you just finished working pretty hard so you probably deserve a break. Besides, you’ve got a few errands to run and Oprah’s on later.

Do you see what’s going on here?

The immediate gratification of “instant freedom” makes entrepreneurs complacent. They feel like they’re already a third of the way towards scoring the hat trick, even though they haven’t even started their company.

As time goes by, the entrepreneur starts to become more and more aware of the lack of wealth. The bills are piling up – most likely due to all that enjoyed freedom. Soon, even “sanity” looks marginal, as the stress of surviving as an utterly free entrepreneur takes it’s toll.

Freedom can cost an entrepreneur any shot at wealth and sanity.

Freedom can destroy a creative entrepreneurs ability to perform as they refuse to commit to deadlines and daily output. “Why do that when it feels so much like a job?!” they cry, in vain.

Freedom shatters the service-based business owner when they miss out on helping clients in a timely manner – it happens (all the time) because the entrepreneur is off “being free” instead of working.

Freedom cripples all businesses when it entices entrepreneurs to avoid planning, structure and discipline.

In your effort to enjoy instant freedom, you rob your business of the ingredients it needs to create real freedom and wealth.

It’s time to redefine “Freedom”

If any of the above sounds familiar, it’s time to have a practical look at the way you define the concept of Freedom.

Is the freedom you pursue easily accessible and under-rewarding? Does it feel cheap and fast, like a McDonald’s meal that leaves you with McRegret?


Is your freedom earned through smarts and sweat? Is it nourishing? Does it take you places in style, like a private jet with an in-flight pastry chef?

One of these two Freedoms is built on a foundation of structure, discipline and hard work. The other is built on nothing and comes at an enormous price.

One freedom erodes wealth and the other creates it by necessity. One reinforces sanity while the other erodes it.

What kind of freedom are you pursuing?

Most wannabe entrepreneurs are selling their chance at a hat trick short, by opting for the easy gratification. They fear the commitment required to earn the real, fulfilling freedom – the stuff with foundation.

Instead, they cling to a dream of “lifestyle” and four hour work weeks. They even tell their friends and family that their mediocre performance is justified by all the glorious freedom they enjoy.

Then, when alone, such entrepreneurs swallow guilty bile as they contemplate a difficult future while regretting a wasted past.

Here’s my advice: Define the freedom you really want. Then pursue it voraciously, without stopping to enjoy cheap substitutes until you win the real stuff.

That is all.


+ Add Comment
  1. For me, it’s the freedom of taking ownership of *every* *single* *one* of my actions.

    I am the only person on whom I can depend for making anything happen with my business.

    That kind of freedom….rocks. But it requires an incredible amount of both maturity and responsibility. Took me years to seize that…

  2. I see this a LOT in people who choose to become freelancers. They don’t want to create a freelance business… they want to shed obligation and responsibility and tra-la-la off into the sunset doing whatever they feel like.

    Freelancing isn’t freedom – at least, not in the tra-la-la sense. I believe it gives you the freedom of choice and of control of your own life. You DO have obligations and responsibilities – but as you pointed out, you can choose when and where to accomplish those tasks and control which tasks take priority.

    I’ve never lived to the illusion that I have complete freedom – my business, despite being mine to control, needs attention and has demands on my time. But I can choose to take Wednesdays off instead of weekends, I can choose to start work at 6am and end at 2pm instead of working 9 to 5, and I can control which priorities help me achieve better success.

    That’s freedom. At least, it’s the freedom that helps me attain my ultimate goals.

    1. AND, James (cos here’s the kicker)… your business has a foundation of hard work and awesomeness that *allows* you to drop everything to go be with family, road trip or skate. Without anything falling apart. Without any need to regret time spent lazing around.

      T’ain’t so for most others. I’d tell you to count yourself lucky… if I didn’t already know that luck has nothing to do with it.

    2. I’m jumping in to put another voice to the message. As one who once wasted the apparent freedom, I can tell you, the “real” freedom is harder earned, yet so much more satisfying. Self-sabotage, on the day you realize that’s what it is, will suck you dry on energy, emotion, and passion. Not to mention finances.

      Like James says, it isn’t freedom from obligation that true entrepreneurs seek. It’s freedom of choice and control. Freedom to set big goals and achieve them!

    1. Good that this one hit the mark Martin, but honestly… I’m still hanging out for some comments from the people who I was really aiming this at.

      My clients all know I sometimes leave ’em messages here hehehe 😛

  3. Peter,
    The analogy of McDonald’s v. the pastry chef in a private jet hits the target for me, describing the different “feel” of two kinds of freedom. Not that I am a pastry or private jet kind of gal, mind you, but I’ve been known to eat a lot of junk food because real nourishment seemed too far away, the escape velocity too great. What I enjoy now is starting to trust that I can know when I have done enough for a day and now I can grab a blanket, a bottle of wine, and some good finger food and picnic with my beloved in the park. Maybe the park is in Paris, Queensland, or Buenos Aires instead of Durham NC, mind you. 😉

    1. Hey Cory! Love the picnic re-defining of the metaphor! That’s what it’s all about – finding ways to enjoy freedom that is actually *significant* to you, rather than just easily accessible.

      You’ve made me think (totally off topic), but I’d guess the same thing actually really does happen with food! Some people put instantly gratifying stuff in their bodies… others enjoy fewer but better quality eating experience.

      It’s been my policy, for the last few years, to only ever eat dessert if what’s on offer is both rare AND remarkable. That one rule dropped at least 5KG for me…

  4. Hi Peter,

    Important post you wrote here! Everything in life is a trade-off. Freedom from the cubicle may mean less freedom at night when a freelancer attends networking events. Self-employment that works requires one to still work at it. We just get to call more of the shots or call them in ways that speak to us.

    Love your last line: “Define the freedom you really want. Then pursue it voraciously, without stopping to enjoy cheap substitutes until you win the real stuff.”

    For me, being out of the cubicle cage has been worth the price of admission. I used to feel like a caged animal and start “pacing” around 3:00. Just don’t think it’s normal to incarcerate people all day like that. How can that get you the best from your employees?

    Thx, Giulietta

    1. Hi Giulietta,

      All great points. It’s a lot tougher to enforce the discipline required when you are the only boss – after all, whos to stop you from blowing off the networking event?

      Glad you got out of the cage! 🙂

  5. Hi Peter,

    great post!!!

    Just few days ago I was thinking about “freedom” because of something that happened to me (my coach dumped me, basically… or better yet my coach dumped all her clients in order to “do something new” and yadda yadda).

    In the exasperate pursue of freedom we oftentimes forgot one thing, accountability and the duty to care about others. True, we don’t need to do things to please other people but we should strive to be ourselves while at the same time keeping the backlash on others at its minimum.

    Do you think these things I wrote make sense? Or is it just because of my medical background? And, if so, do you think that applies to other mental health professionals as well?

    I’m curious to pick your mind about this!

    1. In terms of caring for others, I think that that is a little separate to the Freedom ideas here. Our empathy is basically determined by our values… but we all look for freedom regardless of what flavor of personality we have.

      You’re spot on about the accountability – that’s where the pursuit of sucky freedom really burns entrepreneurs. 🙂

      1. I beg to differ from your assessment, Peter!

        I find freedom to be connected to caring for others. Individual freedom (ie doing one’s good even when it goes against somebody else) is different from a win-win choice (ie taking the fairest option to the highest amount of people). For example, an entrepreneur can decide to dump a client without a referral just because s/he “feels like changing focusin his/her business”. Another example is, an entrepreneur who does something legally allowed but ethically questionable just because s/he doesn’t belong to a medical board, bar association or other ethical body that might punish him/her, feeling “free” to misbehave as long as s/he doesn’t get any consequence out of it.

        Ultimately, relativism fosters the same sense of warped freedom… if everything is relative (and there’s no right and no wrong) than the person taking the decision isn’t accountable to anybody but him/herself. It’s empathy (ie the mirror neurons) that prevents people from harming another person, not values… values are built around such empathy… biology first, and lower structures in the brains are the ones that takes over in survival mode 😉

        Somehow mental health professionals are taught in school to ponder the repercussions of their actions on their clients before deciding to take an action… If you don’t want a patient anymore but the patient has an urgent problem you take him/her in no matter how much you dislike him, and when you decide to dump him/her you can’t do it without referring him to somebody else. This is sorely missing in the behaviours of entrepreneurs who don’t come from the mental health field.

        1. Rosanna, I think we’re on two different wavelengths here – I certainly don’t disagree with your comments re: the origin of empathy, although I’m not sure how the “biology first” thing is relevant. As a secret, uncover fu-fu’er I could definitely argue the case for psychology affecting biology! But yeah, that’s really not what this post is about.

          I’m talking about the personal freedom entrepreneurs get to enjoy by not being accountable to the usual 9-5 “rules”. Certainly, most entrepreneurs could benefit from caring more about their customers and ensuring they get great treatment when they’re “dropped” or whatever.

          Of course, most businesses don’t have quite the same (dependent) relationship that a mental health professional has with his/her clients. If my favorite cafe closes, I’m not going to lose much sleep over finding a new one.

          … well, maybe a little 😛

          1. It also depends on culture! In some cultures it’s ok to have a just a “professional” relationship with a service provider. In others, it is socially sanctioned.

            The freedom I was talking about (and I would think you were referring to it too, but I must have gotten you wrong) is the one of the entrepreneur deciding to self-determine and be in touch and consistent with himself and his/ values, letting THEM run the show as opposed to societal norms. For this reason, I thought you might also want to discuss the lack of freedom that comes with needing to feel unconstrained in order to experience, well, freedom (in fact my comments were going in that direction just to add to your blog entry – if a comment doesn’t add it is my policy not to post *wink*).

            So the bottom line of what I was trying to add is… depending on which “freedom” framework one chooses, external “rules” might have more (or less) sense and an impact on his/her entrepreneurial freedom. So it’s particularly important not to fall for stereotypes and think “Because I want to be “free” I should fit into the “original and unruly” category” or “Because I want to be regular and reliable, I should fit right in with the 9-5 schedule”.

            In both cases, too often this is not real freedom but rather doing something in fear of being mislabeled.. the free person doesn’t want to be thought of as conformist, the conformist person doesn’t want to look or sound odd. It’s the value that we choose to attach to those choices that deludes us into thinking we are more (or less) free when we take them.

            So you are right in this, psychology plays a big part in what label we assign to “freedom”. As far as I am concerned, I think that the ONLY freedom is to give up the illusion to manipulate the impression that people have of us and…drop the mask – whatever the mask is.

            And – sadly enough – “being free” is too often but a mask.

            Good night!

  6. Peter, great post and I couldn’t agree more. I help health care professionals grow their practices and most were sold the line that once they got their degree on the fancy license they could hang out a shingle and the clients (and money) would come flowing in. Many don’t realize they need to work some evenings and weekends (when working folk can get to an appt), offer amazing customer service (because clients have choices) and keep up with the complex administrative side of their business (because otherwise they won’t get paid).

    We can make our own schedule and try to take a break from the mundane parts of running a business, but if we aren’t doing a great job giving people need/want or solve their pain we’re sunk. And that level of productivity needs more than a McWork ethic.

    1. Susan, this is a great example – that health care niche might as well be a microcosm for ALL entrepreneurialism. That instant freedom is the lie that most newbie business owners initially got excited by too.

      McWork ethic! LOL 😉

  7. For me, freedom isn’t about being able to do whatever you want, but being able to do what you love.

    And when you love something the HARD WORK and SELF DISCIPLINE should come with the package. Otherwise, you don’t really care about the thing as much as you think you do.

    If you truly care about your projects…then you put in the work to make them work. Why? Because it’s your ikigai or “reason for living” – and no man is free without one.

    What you describe Pete is a real concern for anyone who is self-employed or an entrepreneur. It is very easy to fall into that kind of freedom trap.

    Wise words and very well-written!

    1. Thanks for the great feedback Steven 🙂

      Your comments on passion valuable – that’s one of the biggest oversights of this post: If you really care passionately about your business, that shitty instant-freedom won’t be half as appealing.

      1. Reminds me of a conversation I had last week with someone. They say, “You’re always working. Why don’t you do something FUN?!”

        And I looked up in surprise. “But my work IS fun.” I couldn’t think of anything I would’ve rather been doing.

        I think it pays off, too. Just two nights ago, my wee one was snuggling up for bed and she said, “When I grow up, I’m going to have a job I like. Just like you.”

        *warm fuzzies*

  8. Awesome post Pete!

    I totally agree with Steven’s comment – doing what you love, not whatever you want. Although – the two should hopefully be the same thing the majority of the time.

    Something I should definitely think more seriously about!

    1. What up Chris!

      Good to see you comment here dude. From what I know about what you’re doing, Instant Freedom isn’t something you need to worry about for a whiles yet… you crazy academic 😛

  9. I’m particularly intrigued by the posts from the medical/mental health professionals here. Where my medical practice is concerned, being “free” means that I get to care for people in accordance with my values (and hopefully THEIRS), not in lock step with a medical institution “group think” or by a productivity quota set by bean counters and executives. That means…I am responsible for EVERY decision made under my roof, whether it is my decision, or the decision of a staff member in my employ. The buck stops with me (gulp) and every minute of every day, my decisions impact lives in the most crucial and intimate ways. there is not (or not yet) an option for me to automate myself and hand all decision making over to a virtual assistant and do email medicine from a hammock in Bali. While that’s an enviable lifestyle, I unfortunately feel the “freest” when I am up to my eyeballs in personal, hands on, interconnections. My challenge now is to know when the job is as done as it can be ethically and to limit how much of my life and energy flows into the care of others. because I set out to be “free” in that critical, ultra-accountable way, I am now “free” to consider just how much of myself I give over to that , and how much I reserve for my own self care and the care of my loved ones. That is not something I could ever have aspired to in someone else’s practice model.

    1. Cory,

      Thanks for adding this comment to the mix – your profession forces you to approach entrepreneurialism (and such concepts as “freedom”) from a unique and refreshing point of view.

      I think it’s interesting that you define freedom as a form of control – or, volition over how you spend your time. It’s what you choose to DO with your freedom that makes you different.


  10. Hi Peter,

    Great post. I recently made the leap to go out on my own. Much of what you said rings true to me. It is tempting sometimes to go run an errand or become distracted in some other way. Fortunately hard work and discipline can ward off those habits. The instant freedom is enjoyable though. I like being able to work at the times when I’m most productive and on the tasks I feel are priority. But I agree with some of the other readers in that the freedom is different when you are doing something you enjoy and take ownership. Lifestyle is part of it, but ultimately probably not enough for the long-term.

    Reading your post was a great reminder to check for complacency. I think freedom with foundation is necessary to remain motivated, but remembering what it was like working for former bosses never hurts 🙂



    1. Hey Brandon! Thanks for stopping by.

      You make good points – I think there IS a lot to be thankful for, just working on your own… but I also think it’s up to us, as entrepreneurs, to do something significant with the opportunities we have.

  11. Hi Pete,

    Great post. I just got around to reading it ‘cos I been back working for ‘the man’ again.
    You nailed it with the responsibility and discipline to drive for your ultimate reward and not the quickie, instant gratification one. But I’ve had a PIG issue for a long time now – Problem with Instant Gratification.
    But is it so like the McDonalds followed with a double helping of the McRegrets…

    Keeping Rocking On!!!

  12. I completly agree with you. The Feel productive working from 10pm to 3am? Screw office hours – do it! simply… I just loved.
    Perfect article!

Leave a Comment

Outsource your battle for Focus and Productivity

Commit Action’s Executive Aide service helps business owners become the highest leverage version of themselves possible.

Visit Peter’s other business